Chemoselective deprotection and functional group interconversion of ring-fused 2 N,3 O-oxazolidinones of N-acetyl- d-glucosamine

Abstract

These studies describe the chemoselective deprotection of trans-fused 2 N,3 O-oxazolidinone derivatives of N-acetyl-β- d-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2 N,3 O-oxazolidinone derivatives of N-acetyl- d-glucosamine.